Enzymatic glycosylation of vancomycin aglycon: completion of a total synthesis of vancomycin and N- and C-terminus substituent effects of the aglycon substrate

scientific article

Enzymatic glycosylation of vancomycin aglycon: completion of a total synthesis of vancomycin and N- and C-terminus substituent effects of the aglycon substrate is …
instance of (P31):
scholarly articleQ13442814

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P356DOI10.1021/OL501568T
P932PMC publication ID4084835
P698PubMed publication ID24954524
P5875ResearchGate publication ID263323765

P2093author name stringChristopher T Walsh
Dale L Boger
Karen C Collins
Yiqing Feng
Atsushi Nakayama
James C Collins
Akinori Okano
P2860cites workA redesigned vancomycin engineered for dual D-Ala-D-ala And D-Ala-D-Lac binding exhibits potent antimicrobial activity against vancomycin-resistant bacteriaQ24607630
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Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA.Q34968575
Vancomycin analogues active against vanA-resistant strains inhibit bacterial transglycosylase without binding substrateQ35021822
Synthesis and stereochemical determination of complestatin A and B (neuroprotectin A and B)Q35552210
Total synthesis of [Ψ[C(═S)NH]Tpg4]vancomycin aglycon, [Ψ[C(═NH)NH]Tpg4]vancomycin aglycon, and related key compounds: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac bindingQ35683194
Glycopeptide antibiotics: from conventional molecules to new derivativesQ35752864
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Total synthesis and evaluation of [Psi[CH2NH]Tpg4]vancomycin aglycon: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac bindingQ36980378
Total synthesis of chloropeptin II (complestatin) and chloropeptin I.Q37438553
Vancomycin and related antibioticsQ40245599
Vancomycin resistance: decoding the molecular logicQ40856100
Structure-activity relationships of vancomycin-type glycopeptide antibioticsQ40863295
Structural modifications of glycopeptide antibioticsQ41287183
Tandem action of glycosyltransferases in the maturation of vancomycin and teicoplanin aglycones: novel glycopeptides.Q43569384
First and second generation total synthesis of the teicoplanin aglyconQ43677371
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The structural basis for induction of VanB resistanceQ44083371
Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptidesQ44260076
A new and improved method for deglycosidation of glycopeptide antibiotics exemplified with vancomycin, ristocetin, and ramoplaninQ44366613
Partitioning the loss in vancomycin binding affinity for D-Ala-D-Lac into lost H-bond and repulsive lone pair contributionsQ44531782
A Programmable One‐Pot Oligosaccharide Synthesis for Diversifying the Sugar Domains of Natural Products: A Case Study of VancomycinQ44610502
Genetic analysis of a high-level vancomycin-resistant isolate of Staphylococcus aureusQ44674318
Total synthesis of the ristocetin aglyconQ44821612
Tailoring of glycopeptide scaffolds by the acyltransferases from the teicoplanin and A-40,926 biosynthetic operonsQ45233945
Vancomycin analogues containing monosaccharides exhibit improved antibiotic activity: a combined one-pot enzymatic glycosylation and chemical diversification strategyQ46612271
A systematic investigation of the synthetic utility of glycopeptide glycosyltransferasesQ46619870
Vancomycin derivatives that inhibit peptidoglycan biosynthesis without binding D-Ala-D-Ala.Q54099400
A General Strategy toward S-Linked GlycopeptidesQ62603835
Plasmid-mediated resistance to vancomycin and teicoplanin in Enterococcus faeciumQ70057223
Model for antibiotic optimization via neoglycosylation: synthesis of liponeoglycopeptides active against VREQ80468522
A practical method for the stereoselective generation of beta-2-deoxy glycosyl phosphatesQ80494849
P433issue13
P407language of work or nameEnglishQ1860
P921main subjectvancomycinQ424027
glycosylationQ898365
P304page(s)3572-3575
P577publication date2014-06-23
P1433published inOrganic LettersQ2396276
P1476titleEnzymatic glycosylation of vancomycin aglycon: completion of a total synthesis of vancomycin and N- and C-terminus substituent effects of the aglycon substrate
P478volume16

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cites work (P2860)
Q59809615Chemoenzymatic Approach toward the Synthesis of 3-O-(α/β)-Glucosylated 3-Hydroxy-β-lactams
Q38684292In Vitro Reconstitution of OxyA Enzymatic Activity Clarifies Late Steps in Vancomycin Biosynthesis.
Q90684544N-Terminus Alkylation of Vancomycin: Ligand Binding Affinity, Antimicrobial Activity, and Site-Specific Nature of Quaternary Trimethylammonium Salt Modification
Q40192107Peripheral modifications of [Ψ[CH2NH]Tpg4]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics
Q39077230Rapid access to glycopeptide antibiotic precursor peptides coupled with cytochrome P450-mediated catalysis: towards a biomimetic synthesis of glycopeptide antibiotics.
Q57581070Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent
Q40504486Reengineering Antibiotics to Combat Bacterial Resistance: Click Chemistry [1,2,3]-Triazole Vancomycin Dimers with Potent Activity against MRSA and VRE.
Q46236467The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry-Biology Interface.
Q39258608Total Syntheses of Vancomycin-Related Glycopeptide Antibiotics and Key Analogues
Q35224649Total syntheses and initial evaluation of [Ψ[C(═S)NH]Tpg⁴]vancomycin, [Ψ[C(═NH)NH]Tpg⁴]vancomycin, [Ψ[CH₂NH]Tpg⁴]vancomycin, and their (4-chlorobiphenyl)methyl derivatives: synergistic binding pocket and peripheral modifications for the glycopeptide
Q34282738Total synthesis of [Ψ[C(═NH)NH]Tpg(4)]vancomycin and its (4-chlorobiphenyl)methyl derivative: impact of peripheral modifications on vancomycin analogues redesigned for dual D-Ala-D-Ala and D-Ala-D-Lac binding

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